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Showing NP-Card for n-hydroxy-2-methylpropanamine (NP0197243)

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Record Information
Version2.0
Created at2022-09-04 15:28:00 UTC
Updated at2022-09-04 15:28:00 UTC
NP-MRD IDNP0197243
Secondary Accession NumbersNone
Natural Product Identification
Common Namen-hydroxy-2-methylpropanamine
DescriptionN-hydroxy-2-methylpropanamine, also known as isobutylhydroxylamine or N-(2-methylpropyl)-hydroxylamine, belongs to the class of organic compounds known as n-organohydroxylamines. These are organic compounds comprising the hydroxylamine functional group, with the general structure R1ON(R2)R3 (R1,R3=H, organyl; R2 = organyl). N-hydroxy-2-methylpropanamine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. n-hydroxy-2-methylpropanamine is found in Streptomyces viridifaciens. n-hydroxy-2-methylpropanamine was first documented in 1997 (PMID: 8990292). Based on a literature review a small amount of articles have been published on N-hydroxy-2-methylpropanamine (PMID: 12688722) (PMID: 18451033) (PMID: 9056232) (PMID: 9287340).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0197243 (n-hydroxy-2-methylpropanamine)


  Mrv1652309042217282D          

  6  5  0  0  0  0            999 V2000
    2.4750   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
M  END
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3D MOL for NP0197243 (n-hydroxy-2-methylpropanamine)

     RDKit          3D

 17 16  0  0  0  0  0  0  0  0999 V2000
   -0.9368   -1.4170    0.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7377   -0.0163   -0.4490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3166    0.9915    0.4957 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7149    0.2212   -0.7623 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5673    0.0770    0.3995 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8405    0.3113    0.0014 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9285   -1.5451    0.5517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1149   -1.7208    0.7516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8860   -2.0963   -0.8113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2894    0.0394   -1.4110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8824    1.9815    0.3511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2743    0.6408    1.5665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4156    1.0671    0.2625 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8544    1.2290   -1.2013 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0122   -0.5111   -1.5408 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3361    0.8686    1.0702 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4567   -0.1208    0.6386 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  1  7  1  0
  1  8  1  0
  1  9  1  0
  2 10  1  0
  3 11  1  0
  3 12  1  0
  3 13  1  0
  4 14  1  0
  4 15  1  0
  5 16  1  0
  6 17  1  0
M  END
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3D SDF for NP0197243 (n-hydroxy-2-methylpropanamine)


  Mrv1652309042217282D          

  6  5  0  0  0  0            999 V2000
    2.4750   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0197243

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CNO

> <INCHI_IDENTIFIER>
InChI=1S/C4H11NO/c1-4(2)3-5-6/h4-6H,3H2,1-2H3

> <INCHI_KEY>
NDCGVLJXFQKXOF-UHFFFAOYSA-N

> <FORMULA>
C4H11NO

> <MOLECULAR_WEIGHT>
89.138

> <EXACT_MASS>
89.084063978

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
10.348553925986087

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-(2-methylpropyl)hydroxylamine

> <JCHEM_LOGP>
0.7274828620000002

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.10548727347553

> <JCHEM_PKA_STRONGEST_BASIC>
5.204968526436482

> <JCHEM_POLAR_SURFACE_AREA>
32.26

> <JCHEM_REFRACTIVITY>
35.9204

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
N-(2-methylpropyl)hydroxylamine

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0197243 (n-hydroxy-2-methylpropanamine)

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PDB for NP0197243 (n-hydroxy-2-methylpropanamine)
HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       4.620  -2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.850  -1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.620  -0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       1.540   0.000   0.000  0.00  0.00           N+0
HETATM    6  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5                                                            
MASTER        0    0    0    0    0    0    0    0    6    0   10    0
END

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3D PDB for NP0197243 (n-hydroxy-2-methylpropanamine)
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SMILES for NP0197243 (n-hydroxy-2-methylpropanamine)
CC(C)CNO
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INCHI for NP0197243 (n-hydroxy-2-methylpropanamine)
InChI=1S/C4H11NO/c1-4(2)3-5-6/h4-6H,3H2,1-2H3
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Synonyms
ValueSource
IsobutylhydroxylamineChEBI
N-(2-Methylpropyl)-hydroxylamineChEBI
N-(2-Methylpropyl)hydroxylamineChEBI
N-(Isobutyl)hydroxylamineChEBI
N-HydroxyisobutylamineChEBI
N-IsobutylhydroxylamineChEBI
Chemical FormulaC4H11NO
Average Mass89.1380 Da
Monoisotopic Mass89.08406 Da
IUPAC NameN-(2-methylpropyl)hydroxylamine
Traditional NameN-(2-methylpropyl)hydroxylamine
CAS Registry NumberNot Available
SMILES
CC(C)CNO
InChI Identifier
InChI=1S/C4H11NO/c1-4(2)3-5-6/h4-6H,3H2,1-2H3
InChI KeyNDCGVLJXFQKXOF-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Streptomyces viridifaciensLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-organohydroxylamines. These are organic compounds comprising the hydroxylamine functional group, with the general structure R1ON(R2)R3 (R1,R3=H, organyl; R2 = organyl).
KingdomOrganic compounds  
Super ClassOrganic nitrogen compounds  
ClassOrganonitrogen compounds  
Sub ClassN-organohydroxylamines  
Direct ParentN-organohydroxylamines  
Alternative Parents
Substituents
  • N-organohydroxylamine
    • 

  • Organic oxygen compound
    • 

  • Organopnictogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.73ChemAxon
pKa (Strongest Acidic)16.11ChemAxon
pKa (Strongest Basic)5.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area32.26 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity35.92 m³·mol⁻¹ChemAxon
Polarizability10.35 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID7822302  
KEGG Compound IDNot Available
BioCyc IDCPD-14697  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9543329  
PDB IDNot Available
ChEBI ID131928  
Good Scents IDNot Available
References
General References
  1. Tao T, Alemany LB, Parry RJ: Valanimycin biosynthesis: investigations of the mechanism of isobutylhydroxylamine incorporation. Org Lett. 2003 Apr 17;5(8):1213-5. doi: 10.1021/ol0340989. [PubMed:12688722  ] 
  2. Garg RP, Qian XL, Alemany LB, Moran S, Parry RJ: Investigations of valanimycin biosynthesis: elucidation of the role of seryl-tRNA. Proc Natl Acad Sci U S A. 2008 May 6;105(18):6543-7. doi:  10.1073/pnas.0708957105. Epub 2008 May 1. [PubMed:18451033  ] 
  3. Parry RJ, Li W, Cooper HN: Cloning, analysis, and overexpression of the gene encoding isobutylamine N-hydroxylase from the valanimycin producer, Streptomyces viridifaciens. J Bacteriol. 1997 Jan;179(2):409-16. doi: 10.1128/jb.179.2.409-416.1997. [PubMed:8990292  ] 
  4. Parry RJ, Li W: Purification and characterization of isobutylamine N-hydroxylase from the valanimycin producer Streptomyces viridifaciens MG456-hF10. Arch Biochem Biophys. 1997 Mar 1;339(1):47-54. doi: 10.1006/abbi.1996.9857. [PubMed:9056232  ] 
  5. Parry RJ, Li W: An NADPH:FAD oxidoreductase from the valanimycin producer, Streptomyces viridifaciens. Cloning, analysis, and overexpression. J Biol Chem. 1997 Sep 12;272(37):23303-11. doi: 10.1074/jbc.272.37.23303. [PubMed:9287340  ] 
  6. LOTUS database [Link]